Synthesis and SAR studies of pyrazole-3-carboxamides and -thioureides including chiral moiety: Novel candidates as antibacterial agents

Ishak Bildirici, Adnan Cetin, Nurettin Menges, Yusuf Alan

Abstract


A series of tetra substitute pyrazole-3-carboxamides (3a-c) and pyrazole-3-carboxthioureides (6a-c) were synthesized and their structures were characterized by IR, NMR, and Elemental analysis. The antibacterial potential against specific Gram-positive and Gram-negative strains and antifungal activities of all novel compounds were investigated. The structure-activity relationships (SAR) studies and some theoretical parameters (CLogP, CMR, PSA, ESP) of the compounds were carried out on these two pyrazole derivatives. Pyrazole-3-carboxilate (2) was used for the synthesis of carboxamide derivatives. The reactions of pyrazole-3-isothiocyanate (5) with appropriate chiral amino alcohols were utilized for synthesizing of thioureide derivatives. Both of these pyrazole derivatives including chiral moiety were exhibited pronounced antibacterial activities. According to the present in vitro study, some of our promising compounds might be new candidates as new generation antibacterial drug.

Keywords


biological activity; chiral amino alcohols; pyrazole; heterocyclic compounds

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DOI: https://doi.org/10.2298/JSC170313029B

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